CA2276213A1 - Methode pour synthetiser des oligonucleotides phosphorothioates - Google Patents
Methode pour synthetiser des oligonucleotides phosphorothioates Download PDFInfo
- Publication number
- CA2276213A1 CA2276213A1 CA002276213A CA2276213A CA2276213A1 CA 2276213 A1 CA2276213 A1 CA 2276213A1 CA 002276213 A CA002276213 A CA 002276213A CA 2276213 A CA2276213 A CA 2276213A CA 2276213 A1 CA2276213 A1 CA 2276213A1
- Authority
- CA
- Canada
- Prior art keywords
- phosphorothioate oligonucleotides
- synthesizing phosphorothioate
- synthesizing
- phosphoramidite intermediates
- oligonucleotides
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract 3
- 108091034117 Oligonucleotide Proteins 0.000 title abstract 2
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 title abstract 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 title abstract 2
- 230000002194 synthesizing effect Effects 0.000 title 1
- 239000000543 intermediate Substances 0.000 abstract 2
- 150000008300 phosphoramidites Chemical class 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/775,011 | 1996-12-27 | ||
| US08/775,011 US6172217B1 (en) | 1996-12-27 | 1996-12-27 | Method of synthesizing phosphorothioate oligonucleotides |
| PCT/US1997/023601 WO1998029427A1 (fr) | 1996-12-27 | 1997-12-12 | Methode pour synthetiser des oligonucleotides phosphorothioates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2276213A1 true CA2276213A1 (fr) | 1998-07-09 |
| CA2276213C CA2276213C (fr) | 2003-12-02 |
Family
ID=25103044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002276213A Expired - Fee Related CA2276213C (fr) | 1996-12-27 | 1997-12-12 | Methode pour synthetiser des oligonucleotides phosphorothioates |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US6172217B1 (fr) |
| EP (1) | EP0948512B1 (fr) |
| JP (1) | JP2000511933A (fr) |
| KR (1) | KR100458979B1 (fr) |
| AT (1) | ATE278702T1 (fr) |
| AU (1) | AU721750B2 (fr) |
| CA (1) | CA2276213C (fr) |
| DE (1) | DE69731112T2 (fr) |
| WO (1) | WO1998029427A1 (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6172217B1 (en) * | 1996-12-27 | 2001-01-09 | Isis Pharmaceuticals Inc. | Method of synthesizing phosphorothioate oligonucleotides |
| FR2803848B1 (fr) * | 2000-01-19 | 2002-02-15 | Adir | Nouveaux derives de benzenesulfonamide, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DE10041539A1 (de) * | 2000-08-24 | 2002-03-07 | Febit Ferrarius Biotech Gmbh | Neue Amiditderivate zur Synthese von Polymeren auf Oberflächen |
| US20040198640A1 (en) * | 2003-04-02 | 2004-10-07 | Dharmacon, Inc. | Stabilized polynucleotides for use in RNA interference |
| KR101147147B1 (ko) * | 2004-04-01 | 2012-05-25 | 머크 샤프 앤드 돔 코포레이션 | Ｒｎａ 간섭의 오프 타겟 효과 감소를 위한 변형된폴리뉴클레오타이드 |
| US7923206B2 (en) * | 2004-11-22 | 2011-04-12 | Dharmacon, Inc. | Method of determining a cellular response to a biological agent |
| US7935811B2 (en) | 2004-11-22 | 2011-05-03 | Dharmacon, Inc. | Apparatus and system having dry gene silencing compositions |
| US7923207B2 (en) | 2004-11-22 | 2011-04-12 | Dharmacon, Inc. | Apparatus and system having dry gene silencing pools |
| WO2008036841A2 (fr) | 2006-09-22 | 2008-03-27 | Dharmacon, Inc. | Complexes d'oligonucléotides tripartites et procédés de silençage de gènes par interférence arn |
| KR100886139B1 (ko) * | 2007-11-13 | 2009-02-27 | 주식회사 삼천리제약 | 올리고뉴클레오타이드의 제조방법 |
| US8188060B2 (en) | 2008-02-11 | 2012-05-29 | Dharmacon, Inc. | Duplex oligonucleotides with enhanced functionality in gene regulation |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3687808A (en) | 1969-08-14 | 1972-08-29 | Univ Leland Stanford Junior | Synthetic polynucleotides |
| US4500707A (en) | 1980-02-29 | 1985-02-19 | University Patents, Inc. | Nucleosides useful in the preparation of polynucleotides |
| US5132418A (en) | 1980-02-29 | 1992-07-21 | University Patents, Inc. | Process for preparing polynucleotides |
| US4458066A (en) | 1980-02-29 | 1984-07-03 | University Patents, Inc. | Process for preparing polynucleotides |
| US4415732A (en) | 1981-03-27 | 1983-11-15 | University Patents, Inc. | Phosphoramidite compounds and processes |
| US4668777A (en) | 1981-03-27 | 1987-05-26 | University Patents, Inc. | Phosphoramidite nucleoside compounds |
| US4973679A (en) | 1981-03-27 | 1990-11-27 | University Patents, Inc. | Process for oligonucleo tide synthesis using phosphormidite intermediates |
| DE3329892A1 (de) | 1983-08-18 | 1985-03-07 | Köster, Hubert, Prof. Dr., 2000 Hamburg | Verfahren zur herstellung von oligonucleotiden |
| USRE34069E (en) | 1983-08-18 | 1992-09-15 | Biosyntech Gmbh | Process for the preparation of oligonucleotides |
| GB8607265D0 (en) * | 1986-03-24 | 1986-04-30 | London King S College | Protecting groups of organic synthesis |
| DE68929361T2 (de) | 1988-04-27 | 2002-06-20 | Isis Pharmaceuticals, Inc. | Oligoribonukleotid-Derivate und Verwendung davon als Antiviral Arzneimittel |
| US5449769A (en) | 1989-03-06 | 1995-09-12 | Gen-Probe Incorporated | Method and reagent for sulfurization of organophosphorous compounds |
| ATE269870T1 (de) | 1989-10-24 | 2004-07-15 | Isis Pharmaceuticals Inc | 2'-modifizierte oligonukleotide |
| US5212295A (en) | 1990-01-11 | 1993-05-18 | Isis Pharmaceuticals | Monomers for preparation of oligonucleotides having chiral phosphorus linkages |
| US5635488A (en) | 1991-10-15 | 1997-06-03 | Isis Pharmaceuticals, Inc. | Compounds having phosphorodithioate linkages of high chiral purity |
| CA2073500C (fr) | 1990-01-11 | 2008-03-25 | Phillip Dan Cook | Compositions et methodes pour deceler et moduler l'activite de l'arn et l'expression genique |
| US5506212A (en) | 1990-01-11 | 1996-04-09 | Isis Pharmaceuticals, Inc. | Oligonucleotides with substantially chirally pure phosphorothioate linkages |
| US5166387A (en) | 1990-01-12 | 1992-11-24 | Applied Biosystems, Inc. | Method of synthesizing sulfurized oligonucleotide analogs with thiuram disulfides |
| US5151510A (en) | 1990-04-20 | 1992-09-29 | Applied Biosystems, Inc. | Method of synethesizing sulfurized oligonucleotide analogs |
| US5292875A (en) | 1990-04-20 | 1994-03-08 | Lynx Therapeutics, Inc. | Method of synthesizing sulfurized oligonucleotide analogs |
| US5672697A (en) * | 1991-02-08 | 1997-09-30 | Gilead Sciences, Inc. | Nucleoside 5'-methylene phosphonates |
| US5512668A (en) | 1991-03-06 | 1996-04-30 | Polish Academy Of Sciences | Solid phase oligonucleotide synthesis using phospholane intermediates |
| US5525719A (en) * | 1991-08-30 | 1996-06-11 | Chemgenes Corporation | N-protected-2'-O-methyl-and N-protected-3'-O-methyl-ribonucleosides and their phosphoramidite derivatives |
| GB9127243D0 (en) | 1991-12-23 | 1992-02-19 | King S College London | Synthesis of phosphorothioate analogues of oligonucleotides |
| DE69402177T2 (de) | 1993-01-08 | 1997-06-26 | Hybridon Inc | Synthese von dimer-blöcken und ihre verwendung bei der zusammensetzung von oligonukleotiden |
| US6015886A (en) * | 1993-05-24 | 2000-01-18 | Chemgenes Corporation | Oligonucleotide phosphate esters |
| US5571902A (en) | 1993-07-29 | 1996-11-05 | Isis Pharmaceuticals, Inc. | Synthesis of oligonucleotides |
| JPH07157498A (ja) | 1993-12-07 | 1995-06-20 | Sankyo Co Ltd | 短鎖ホスホロチオエート結合オリゴデオキシヌクレオチド |
| WO1995026204A1 (fr) | 1994-03-25 | 1995-10-05 | Isis Pharmaceuticals, Inc. | Stimulation immunitaire par des analogues d'oligonucleotides de phosphorothioate |
| US5405985A (en) | 1994-07-08 | 1995-04-11 | The Goodyear Tire & Rubber Company | Preparation of sulfur-containing organosilicon compounds |
| DE4438918A1 (de) * | 1994-11-04 | 1996-05-09 | Hoechst Ag | Modifizierte Oligonukleotide, deren Herstellung sowie deren Verwendung |
| US6057431A (en) | 1995-03-31 | 2000-05-02 | Drug Delivery System Institute, Ltd. | Amidite derivatives and oligonucleotide derivatives |
| US6172217B1 (en) * | 1996-12-27 | 2001-01-09 | Isis Pharmaceuticals Inc. | Method of synthesizing phosphorothioate oligonucleotides |
| US6649750B1 (en) * | 2000-01-05 | 2003-11-18 | Isis Pharmaceuticals, Inc. | Process for the preparation of oligonucleotide compounds |
-
1996
- 1996-12-27 US US08/775,011 patent/US6172217B1/en not_active Expired - Fee Related
-
1997
- 1997-12-12 WO PCT/US1997/023601 patent/WO1998029427A1/fr active IP Right Grant
- 1997-12-12 KR KR10-1999-7005779A patent/KR100458979B1/ko not_active IP Right Cessation
- 1997-12-12 AU AU59009/98A patent/AU721750B2/en not_active Ceased
- 1997-12-12 EP EP97954597A patent/EP0948512B1/fr not_active Expired - Lifetime
- 1997-12-12 CA CA002276213A patent/CA2276213C/fr not_active Expired - Fee Related
- 1997-12-12 AT AT97954597T patent/ATE278702T1/de not_active IP Right Cessation
- 1997-12-12 JP JP10530137A patent/JP2000511933A/ja not_active Ceased
- 1997-12-12 DE DE69731112T patent/DE69731112T2/de not_active Expired - Fee Related
-
2001
- 2001-01-08 US US09/756,354 patent/US6403781B2/en not_active Expired - Fee Related
-
2002
- 2002-02-06 US US10/068,604 patent/US20020128466A1/en not_active Abandoned
-
2003
- 2003-01-17 US US10/346,659 patent/US6780989B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0948512B1 (fr) | 2004-10-06 |
| AU721750B2 (en) | 2000-07-13 |
| WO1998029427A1 (fr) | 1998-07-09 |
| AU5900998A (en) | 1998-07-31 |
| EP0948512A1 (fr) | 1999-10-13 |
| KR100458979B1 (ko) | 2004-12-03 |
| EP0948512A4 (fr) | 2001-10-24 |
| DE69731112D1 (de) | 2004-11-11 |
| US6172217B1 (en) | 2001-01-09 |
| CA2276213C (fr) | 2003-12-02 |
| US20020128466A1 (en) | 2002-09-12 |
| DE69731112T2 (de) | 2006-02-23 |
| US6780989B2 (en) | 2004-08-24 |
| ATE278702T1 (de) | 2004-10-15 |
| US20030114662A1 (en) | 2003-06-19 |
| US20010003132A1 (en) | 2001-06-07 |
| JP2000511933A (ja) | 2000-09-12 |
| US6403781B2 (en) | 2002-06-11 |
| KR20000069706A (ko) | 2000-11-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL135562A0 (en) | Process for the synthesis of 1,3-diols | |
| AU2792499A (en) | Improved methods for synthesis of oligonucleotides | |
| AU2657095A (en) | Synthesis of oligonucleotides | |
| AU6518398A (en) | Process for producing aldehydes | |
| GB2323183B (en) | A process for diagnosing a plurality of vehicles | |
| AU5441896A (en) | Cooperative oligonucleotides | |
| HUP0004239A2 (en) | Process for synthesizing phosphodiesters | |
| CA2276213A1 (fr) | Methode pour synthetiser des oligonucleotides phosphorothioates | |
| AU1175497A (en) | A class of oligonucleotides, therapeutically useful as antitumoural agents | |
| AU3143695A (en) | Improved methods of detritylation for oligonucleotide synthesis | |
| AU4889396A (en) | Process for producing n-phosphonomethylglycine | |
| HUP9801687A3 (en) | Process for producing nucleic acids | |
| GB2300858B (en) | Process for producing threo-3-(3,4-dihydroxyphenyl)serine | |
| AU8346498A (en) | Method for diagnosing alzheimer disease | |
| AU6186398A (en) | Process for selecting anti-sense oligonucleotides | |
| CA2281471A1 (fr) | Procede de preparation de l'eprosartan | |
| CA2281708A1 (fr) | Procede de preparation de l'eprosartan | |
| AU9017098A (en) | Method for diagnosing alzheimer's disease | |
| HUP9802054A3 (en) | Process for producing 4,4,5,5,5-pentafluor-1-pentanol | |
| ZA962339B (en) | Process for forming tableted high-caustic detergent | |
| SG72861A1 (en) | Process for producing 7-octen-1-al | |
| AU2300995A (en) | A method of synthesizing 5,15-diarylbenzochlorin-7-one compounds | |
| AU5487496A (en) | Combinatorial process for synthesizing azetidinone analogs | |
| HUP9801800A3 (en) | Process for producing 1-pyruvoyl-l-proline | |
| AU3279295A (en) | Process for synthesizing thiocarbonates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |